Keith Savage – Breaking One Career to Build Another

Keith Savage of Traveling Savage is one person who has not allowed societal pressures to stop him from pursuing his career break dreams. He’s not afraid of the unconventional. In fact, his career break plans are quite unconventional! Over the next two years Keith plans to visit 8 countries for a month each (4 months total a year) while beginning a travel writing career. All with the support of his wife, who will remain at home working and taking care of their three cats.

He shares with us what led him to this point in life.

Could you tell me more about what made you decide to take a career break?
The American system of moving from childhood to adulthood usually involves going to college and identifying your future professional pursuit. Going to college also involves far too many parties and tons of interesting “flavors” of coursework. I graduated from school with degrees in creative writing and psychology, but I failed to figure out what I wanted to do with my life. Actually, I think I secretly knew what I’m consciously aware of now: I simply don’t want to do the kind of work that has come to typically define the word.

With no aspirations of seeking higher education after graduation, my liberal arts degrees effectively became little more than proof that I successfully completed undergraduate studies. I was on my own for job hunting, but, by the grace of some long-forgotten god, I managed to land a job as a technical writer at an amazing software company after only a few months. By any estimation this was the best “first job” I could have gotten.

And it only got better. I climbed the ladder and began managing other writers before my second anniversary. Before the end of my third year, I was managing other managers. I was accomplishing goals, reaching new heights, and excelling. It’s hard to say it, but I had never applied myself enough to excel at anything previously. But when the climbing stopped so did the rush, and I was forced to reconcile the fact that while I thrilled at the feeling of advancement I didn’t actually love the work. I had no expectations going into the job, and, after almost seven years, no goals or exit strategy.

I tried a lateral move and a new position in the hope that I would find that fire from my first few years – I really wanted to stay at this amazing company. Alas, it was not to be. There was no way I could live with myself if I “faked it,” doing just enough but never excelling or standing out. I finally forced myself to face the facts. I needed to leave. And if I would sacrifice such a great job then it would have to be for my passions: travel and creative writing.

How did you go about quitting your job?
Once I decided that I would not be satisfied in the position any longer, my wife and I started brainstorming ideas for what I could do. It wasn’t as simple as going to a different company – I loved where I worked and the people I worked with. Ultimately I decided to return to my creative writing roots and meld it with my other love of travel. Identifying my passions has been the hardest part of this entire process, and they are not set in stone. They are fluid, and the best I could do was identify things I enjoyed doing.

I started formulating a plan and then crunched numbers to see how we could work the finances. I forecasted the number of months I needed to work to continue saving and we switched our lifestyle to adhere to a strict budget (which was quite new for us). The months rolled by and we steadily accomplished our monetary goals. Then one day six weeks before my planned departure I spoke with my boss and let her know I was leaving. It was as “simple” as that.

And what were people’s reactions?
People’s reactions have ranged from congratulatory to half-jealous to muted. I haven’t been privy to any wild or outrageous responses. Most people seem to respect me for following my dreams and actually doing the work to make them happen. I’ve been very grateful to have avoided negativity and jealousy from friends and family about my choice, though some have struggled with my giving up a good job. I’ve made it clear that it’s been difficult to come to this conclusion, but that my priorities are not governed by money and as such I can’t allow it to keep me locked into a career that won’t make me happy.

Other comments

Great interview. Keith, I love your plan on 1 month on, 2 months off. It’s quite unique, but I think it will give you a great chance to really get to know the places you’re going to. One of our favorite parts of our RTW was our month in Buenos Aires with an apartment. We loved getting to know the city, the neighborhood, the store owners, restaurants, and bars. It was fantastic, and if we ever go on another long term trip again, we’ll probably employ this strategy instead of constantly being on the move.

Kudos to you for following your dreams. It’s going to be an amazing journey. Is your wife going to be able to join you for any of these adventures? I’d love to know you guys worked this situation out, and how she feels about staying home while you’re on the road? I guess just like any couple who has a spouse with a traveling job. My wife has read what your plan is and said how difficult it would be for her if I was the only one on the road. Just curious as to how you two are dealing with it?

When I backpacked South America for 5-months I left my long-term boyfriend at home. So if you need any advice or tips of how to work a long-distance relationship while your the one traveling and your wife is at home I can definitely help with that.

[…] Briefcase to Backpack asked me a few questions about my career break and I explained how I’m breaking one career and building another, one that’s in line with my values and passions. I’ve got a healthy respect for both of […]

@Adam Glad to hear you’re considering this style of travel. I think it’s going to be great, and it would only be greater if Sarah could join me on these trips. We think that she’ll be able to join me on at least a couple of these trips. Obviously work and her vacation days will factor in the feasibility.

The funny thing is that this idea was originally Sarah’s! The bottom line is that she saw how unhappy and listless I was in my current job, and we’d come to a point where I needed to make a decision – both for my sanity with work and to just be a happier person. So we’re giving it a shot. It’s going to be hard – really hard – for us to be a part for so long. It’s also going to be hard to balance our paths. Obviously I’ll have lots of stories to tell but that might not go over so well if she’s at home working in the office. Care and awareness are crucial.

How are we dealing with it? When you conceive of an idea that is so far in the future, almost everything sounds great. Now that we’re a month away, nerves are setting in and we’re thinking about all the possible negative aspects. But we’re actively trying to stay positive and keep the momentum going. The truth is that this won’t work if either of us is unhappy with the scenario.

Ali on Mon, 4th Oct 2010 11:32 pm

Keith, I love reading about your passion for travel & how you’ve worked to get to this point. I really admire you for following your dreams and leaving a “good” job to make them happen. I’m looking forward to reading about your journey!